2-(RS)-氨基-4-苯基丁酸乙酯盐酸盐 | 93964-79-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 2-(RS)-氨基-4-苯基丁酸乙酯盐酸盐
• 英文名称: ethyl 2-amino-4-phenylbutanoate hydrochloride
• 英文别名: ethyl hyperphenylalaninate hydrochloride；2-(RS)-amino-4-phenylbutyric acid ethyl ester hydrochloride；(+/-)-2-amino-4-phenyl-butyric acid ethyl ester; hydrochloride；2-Amino-4-phenyl-buttersaeure-aethylester; Hydrochlorid；(+/-)-α-aminobenzenebutanoic acid, ethyl ester, monohydrochloride；homophenylalanine ethyl ester hydrochloride；(1-Ethoxy-1-oxo-4-phenylbutan-2-yl)azanium;chloride；(1-ethoxy-1-oxo-4-phenylbutan-2-yl)azanium;chloride
• CAS: 93964-79-5
• 化学式: C₁₂H₁₇NO₂*ClH
• 分子量: 243.733
• InChiKey: PTFKZMFFSIYCOV-UHFFFAOYSA-N

物化性质

• 熔点：
  121-123 °C

计算性质

• 辛醇/水分配系数(LogP)：
  1.93
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  52.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(RS)-氨基-4-苯基丁酸乙酯盐酸盐 在 盐酸 作用下， 以 水 为溶剂， 反应 4.0h， 以1.52 g的产率得到DL-高苯丙氨酸
  参考文献：
  名称：

  通过关键的 Neber 重排合成 [1-13C] 和 [1-15N] 标记的 DL-高苯丙氨酸

  摘要：

  描述了一种涉及关键 Neber 重排的合成路线，用于制备 [1-13C] 和 [1-15N] DL-高苯丙氨酸（2-氨基-4-苯基丁酸），使用适当标记的氰化钠作为其来源同位素标签。这些化合物已制备用于研究甘蓝型油菜中苯乙基硫代葡萄糖苷的生物合成。3-苯基丙醛肟是由高苯丙氨酸形成的初始生物合成产物，也以 15N 标记形式制备。© 1998 John Wiley & Sons, Ltd.

  DOI：

  10.1002/(sici)1099-1344(199801)41:1<29::aid-jlcr50>3.0.co;2-e
• 作为产物：
  描述：

  2-乙酰氨基-2-苯乙基丙二醇二乙酯 在 盐酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 0.5h， 生成 2-(RS)-氨基-4-苯基丁酸乙酯盐酸盐
  参考文献：
  名称：

  New Anthranilic Acid Based Antagonists with High Affinity and Selectivity for the Human Cholecystokinin Receptor 1 (hCCK₁-R)

  摘要：

  The anthranilic acid diamides represent the most recent class of nonpeptide CCK1 receptor (CCK1-R) antagonists. Herein we describe the second phase of the anthranilic acid C-terminal optimization using nonproteinogenic amino acids containing a phenyl ring in their side chain. The Homo-Phe derivative 2 (VL-0797) enhanced 12-fold the affinity for the rat CCK1-R affinity and 15-fold for the human CCK1-R relative to the reference compound 12 (VL-0395). The eutomer of 2 (6) exhibited a nanomolar range affinity toward the human CCK1-R and was at least 400-fold selective for the CCK1-R over the CCK2-R. Molecular docking in the modeled CCK1-R and its validation by site-directed mutagenesis experiments showed that the 6 binding site overlaps that occupied by the C-terminal bioactive region of the natural agonist CCK. Owing to their interesting properties, new compounds provided by this study represent a solid basis for further advances aimed at synthesis of clinically valuable CCK1-R antagonists.

  DOI：

  10.1021/jm200438b

文献信息

• Donor–Acceptor Complex Enables Cascade Radical Cyclization of <i>N</i>-Arylacrylamides with Katritzky Salts
  作者：Yu Lu、Chang-Zhen Fang、Qiang Liu、Bao-Lin Li、Zhi-Xiang Wang、Xiang-Yu Chen

  DOI：10.1021/acs.orglett.1c01758

  日期：2021.7.16

  Cascade radical cyclization of N-arylacrylamides is an attractive method to prepare 3,3-disubstituted oxindoles. As the reported methods often require additives and/or photocatalysts, we herein report an additive- and photocatalyst-free deaminative strategy for their synthesis under mild conditions, enabled by photoactivation of an electron donor–acceptor (EDA) complex. DFT studies indicated that the

  N-芳基丙烯酰胺的级联自由基环化是制备 3,3-二取代羟吲哚的一种有吸引力的方法。由于报道的方法通常需要添加剂和/或光催化剂，我们在此报告了一种在温和条件下合成的无添加剂和无光催化剂的脱氨基策略，通过电子供体 - 受体（EDA）复合物的光活化实现。DFT 研究表明，明确的二甲苯溶剂分子的参与可以大大增强N-芳基丙烯酰胺和卡特里茨基盐之间的 EDA 复合物的光活性。
• Stereoselective and Site-Specific Allylic Alkylation of Amino Acids and Small Peptides via a Pd/Cu Dual Catalysis
  作者：Xiaohong Huo、Rui He、Jingke Fu、Jiacheng Zhang、Guoqiang Yang、Wanbin Zhang

  DOI：10.1021/jacs.7b05460

  日期：2017.7.26

  alkylation of Schiff base activated amino acids and small peptides via a Pd/Cu dual catalysis. A range of noncoded α,α-dialkyl α-amino acids were easily synthesized in high yields and with excellent enantioselectivities (up to >99% ee). Furthermore, a direct and highly stereoselective synthesis of small peptides with enantiopure α-alkyl or α,α-dialkyl α-amino acids residues incorporated at specific sites

  我们报告的席夫碱活化的氨基酸和小肽通过Pd / Cu双重催化的立体选择性和特定位置的烯丙基烷基化。容易地以高收率和优异的对映选择性（高达> 99％ee）合成一系列非编码的α，α-二烷基α-氨基酸。此外，使用该双重催化剂体系完成了在特定位点掺入对映体纯的α-烷基或α，α-二烷基α-氨基酸残基的小肽的直接和高度立体选择性的合成。
• Novel gamma-lactams as beta-secretase inhibitors
  申请人：Thompson A. Lorin

  公开号：US20060046984A1

  公开（公告）日：2006-03-02

  There is provided a series of novel substituted gamma-lactams of Formula (I) or a stereoisomer; or a pharmaceutically acceptable salt thereof, wherein R 1 , R 2 , R 4 , R 5 and R 6 as defined herein, their pharmaceutical compositions and methods of use. These novel compounds inhibit the processing of amyloid precursor protein (APP) by β-secretase and, more specifically, inhibit the production of Aβ-peptide. The present disclosure is directed to compounds useful in the treatment of neurological disorders related to β-amyloid production, such as Alzheimer's disease and other conditions affected by anti-amyloid activity.

  提供了一系列新型取代的γ-内酰胺，化学式为(I)或其立体异构体；或其药用盐，其中R1、R2、R4、R5和R6如本文所定义，它们的药用组合物和使用方法。这些新型化合物抑制β-分泌酶对淀粉样前体蛋白（APP）的加工，更具体地抑制Aβ肽的产生。本公开涉及对β-淀粉样蛋白产生相关的神经系统疾病的治疗有用的化合物，如阿尔茨海默病和其他受抗淀粉样活性影响的疾病。
• Cyclodimerization of 3-phenacylideneoxindolines with amino esters for the synthesis of dispiro[indoline-3,1′-cyclopentane-3′,3″-indolines]
  作者：Ren-Yin Yang、Jing Sun、Ju Xie、Chao-Guo Yan

  DOI：10.1515/hc-2017-0002

  日期：2017.8.28

  Abstract Triethylamine-promoted domino cyclodimerization reaction of 3-phenacylideneoxindolines with amino ester hydrochlorides in acetonitrile afforded substituted dispiro[indoline-3,1′-cyclopentane-3′,3″-indolines] in good yields. The relative configuration of the major diastereoisomers was determined by the X-ray diffraction analysis of three single crystal structures.

  摘要 三乙胺促进 3-phenacylideneoxindolines 与氨基酯盐酸盐在乙腈中的多米诺环二聚反应以良好的收率得到取代的二螺[indoline-3,1'-cyclopentane-3',3"-indolines]。主要非对映异构体的相对构型通过三种单晶结构的 X 射线衍射分析确定。
• Photoinduced Deaminative Alkylation for the Synthesis of γ-Ketoesters via Electron Donor–Acceptor Complex Formation
  作者：Jia-Xin Wang、Wei Ge、Wei-Long Xing、Ming-Chen Fu

  DOI：10.1021/acs.joc.1c02499

  日期：2021.12.17

  Visible-light-induced deaminative alkylation of Katritzky salts with silyl enol ethers has been developed. The reaction can proceed efficiently through electron donor–acceptor complex formation, avoiding the use of precious metal complexes or synthetically elaborate organic dyes. A series of functionalized γ-ketoesters was successfully obtained with good functional group tolerance and compatibility under mild

  已经开发出可见光诱导的卡特里茨基盐与甲硅烷基烯醇醚的脱氨基烷基化。该反应可以通过电子供体-受体络合物的形成有效地进行，避免使用贵金属络合物或合成复杂的有机染料。在温和直接的条件下，成功获得了一系列具有良好官能团耐受性和相容性的功能化γ-酮酯。